


Five Times Sally Fell for Jack (And Jack fell for Sally)

by sherlockholmes-notanamateur (loki_godofmischiefandlies)



Category: The Nightmare Before Christmas (1993)
Genre: Adventure, F/M, Fluff, Friends to Lovers, Friendship, Romance
Language: English
Status: Completed
Published: 2014-07-31
Updated: 2014-07-31
Packaged: 2018-02-11 04:38:24
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,348
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2053905
Author URL: https://archiveofourown.org/users/loki_godofmischiefandlies/pseuds/sherlockholmes-notanamateur
Summary: <blockquote class="userstuff">
              <p>Sally was drawn to Jack from the first moment they met. Her fascination started out as a desire for friendship, but as time went on her feelings grew until she fell in love with the Pumpkin King. </p>
<p>Little does she know that Skeleton Jack has a heart hidden in those bones.</p>
            </blockquote>





	Five Times Sally Fell for Jack (And Jack fell for Sally)

**Author's Note:**

> So I was tinkering with this idea after re-watching The Nightmare Before Christmas. During the final scene, Jack calls Sally his "dearest friend", and while you can definitely tell that they have a friendship, that friendship was never shown developing. So here is the development of that friendship and the love they have for each other. 
> 
> Please note, I do have a bit of headcanon as to how Halloween Town works. It's apparent (well, to me at least) that Jack goes into the real world from 'Jack's Lament' ("and to a guy in Kentucky, I'm Mister Unlucky, and I'm known throughout England and France") but some of the others don't seem to have any real working knowledge of the 'real world'. So...I'm trying to explain it in my own way here. Hope you enjoy!

**-The First Time-**

"Doctor Finkelstein? Doctor?" Jack called, pushing the door open to the lopsided observatory/laboratory that the doctor resided in. The main hall was unusually dark, even for Halloween Town, and Jack frowned deeply as he pressed further into the doctor's domicile. The door slammed shut with a metallic _clang_ behind him, jolting the skeleton ever so slightly from his deep thoughts. Just as his long legs were about to carry him up the first of many stairs that wound up to the top of the building, the whir of the doctor's wheelchair could be heard. 

"Jack my boy, what can I do for you?" Doctor Finkelstein questioned, although he sounded (and looked) wearier than usual. 

"I was simply stopping by to see if you could assist me with a prop for the next Halloween celebration...are you feeling alright?" Jack queried, brows furrowing as he noticed dark shadows etched under the doctor's little glasses. At that question, the doctor perked up a bit and grinned maniacally. 

"I am splendid, absolutely splendid. I just finished a new creation a few days ago. I've been...trying to teach her a few things is all. Would you like to see?" Doctor Finkelstein asked, the grin not fading once. Jack's curiosity was admittedly peaked; the doctor was always inventing new, strange, and often wondrous things. 

"I would be honored." Jack smiled, knowing that it was unusual for the doctor to show off his new creations until they were (at least, in his mind) perfected. The doctor nodded once and then led Jack through a few winding hallways, stopping at the room he often created new life in. Sitting on the table was a young woman with a curtain of red hair, wide, curious eyes, and lovely blue skin littered with stitches. _A ragdoll of a woman_ Jack thought with a wry grin as their eyes met and she gave him a hesitant, lopsided smile. 

"Hello." she said in a soft voice, waving shyly. 

"Hello. I'm Jack Skellington." Jack replied, offering his hand. She took it and shook it almost clumsily, and it grew apparent that she was still not exactly used to having full use of her limbs yet. The doctor watched from a small distance, curious as to how his new creation would react. She had expressed an almost single-minded determination to escape the lab and explore the outside world, something that he knew in his gut she was not ready for, and so he hoped that this interaction would quell her desire for adventure for now. He almost groaned when he saw that spark in her eyes burst into a fully fledged fire and he suddenly regretted the decision to introduce Sally to the most fascinating individual in Halloween Town first. 

"Sally." Sally offered, almost reluctant to release the bony hand in hers; it was the first time she had met or touched someone other than the doctor, and while it was perfectly friendly, it made her crave more. She wanted to see things for herself, but for now...she wanted to get inside this man's skull. She could see the gleam of intelligence in the murky darkness of his orbitals and she was hooked instantly. "What brings you here?" she asked, knowing that it was unusual for the mad scientist to get visitors considering she had been alive for a week now and hadn't seen hide nor horn of another being other than the doctor and, once, just once, Igor. 

"Oh. Right. I needed the doctor's help with something for next Halloween. It's getting harder to scare them, and so I wanted to add a bit of a...surprise to our usual element." Jack smirked, and that intelligent gleam grew. "Skeletons are scary, especially when they're...well, you know," he gestured to himself, "but they're all so comfortable with the grim now that it's near impossible to get a good shriek out of someone if they  _see_ me." Jack explained, almost pouting. Sally chuckled quietly; she had been fully informed that as a citizen of Halloween Town it would one day be her job to assist the Pumpkin King and the Mayor in planning and executing Halloween. They would journey into the outside world if they were deemed scary enough by Jack, or, if not, they would remain within the town to watch the goings-on from afar, adding a bit of magic to the human world through their own performances and deeds to help 'create atmosphere' for their cohorts. Sally's eyes trailed over the bony man's form, and while she could admit that to people outside of the town he would certainly be bone chilling, he may not incite the terror he once did back in, say, the Victorian Era, when people were terrified of death and all its symbols. 

"What about a disguise?" Sally suggested meekly before the doctor even had time to speak. Jack and the doctor both looked at her with a mixture of shock and pleasure (Jack) or annoyance (the doctor). 

"That's actually not a bad idea...a costume of sorts?" Jack questioned. Sally nodded enthusiastically and hopped up from where she had been sitting, wobbling slightly as she adjusted her balance. 

"Yes, exactly. The Doctor told me that they hang all sorts of decorations and things, but that they go largely unnoticed...perhaps you could disguise yourself among the human's decor and then you would have surprise on your side." Sally explained, circling Jack like a vulture and plucking at his pinstripe suit here and there. "We all call you the Pumpkin King...maybe you should  _become_ the Pumpkin King." she smirked. 

"What do you mean?" Jack asked at the same time the Doctor said " _Sally_ " in a warning tone. 

"Well...I'm sure we could fit a pumpkin over your head...a jack o'lantern," they both smirked at that, making the doctor groan again, "and hide your usual clothes under a scarecrow costume. You're certainly skinny enough, they wouldn't know the difference. Then you could jump out at them or follow them or whatever it is you get up to when you're out there." 

Jack gaped for a moment before his fingers came up to tap at his jaw. 

"That is an absolutely brilliant idea Sally." Jack praised, surveying her with new eyes. She was definitely intelligent, and with that intelligence most certainly came rebellion; he could see why the Doctor would be exhausted by her. Sally blushed a darker shade of blue and looked at her shoes shyly. 

"I...t-thank you." she mumbled, unsure of what to do with the praise. 

"No, thank  _you_. I've already got a thousand and one ideas I could run with from that alone." Jack grinned maniacally. "But...I want you to help me with it." 

"What?" both the Doctor and his creation blurted at the same time. 

"I don't know how to sew." Jack mumbled sheepishly, rubbing the back of his skull and offering Sally a tiny, shy smile of his own. She giggled at that and shrugged. 

"I would have to do the work from here but...I'm sure I could whip something together. You'd just have to come by for fittings every once in a while." Sally beamed.

"Of course! I'm sure it will be brilliant too." Jack beamed in return, and both of them had a feeling that they would develop a wonderful friendship in that moment. The doctor cringed again and shook his head at the cowed expressions on the faces of the skeleton and the ragdoll. 

Great, now Jack was giving her ideas too. 

**-The Second Time-**

"Hold  _still_." Sally hissed, practically chasing Jack around the room as he paced around in the scarecrow suit she was trying to tailor. Jack almost growled at her and continued moving. His mind was racing with new ideas, but at the same time it was hedged with a sense of monotony that was driving him insane. 

"I can't." he snapped back as she caught up to him and grabbed at his arm. "Ow!" he yelped when the tip of her sewing needle poked his palm. 

"Sorry." Sally huffed, quickly stitching up the edge of the tattered sleeve. While it was supposed to look messy, she certainly didn't want it to  _be_ messy. Besides, if it wasn't hemmed properly it could fall apart during the night and then Halloween could be ruined. She wasn't about to let that happen, especially not since this was her first contribution to the holiday. 

"It's alright." Jack sighed, feeling suddenly deflated. The monotony washed over him, and Sally was truly the only interesting thing left in Halloween Town at that moment. He thought back over the last few days and realized with a start that Sally was the only one in the town that spoke to him with something other than reverence in her tone. Well, her and the doctor, but the doctor was such an intellectual that Jack doubted he revered anyone but himself. 

"Are you okay?" Sally questioned, turning his bony hand over to examine his palm. Jack was pulled out of his own skull with that and he nodded distractedly. 

"Fine." he mumbled. "Sally...you...you're different." he said. Sally dropped his hand like a hot coal and looked almost wounded. It was one thing to hear all sorts of things from the doctor about how wretched and troublesome she was, but coming from the skeleton...it  _stung_ with an intensity she could not place. 

"I..." she stammered, looking away with slumped shoulders. That was when Jack looked up and he gasped. 

"No. No, no, no, I didn't mean it as a bad thing." he said in a rush, gently placing his hands on her shoulders to turn her around. She was reluctant to meet his eyes, but when she did there was a gentleness softening the dark edges of his orbitals. 

"Then what did you mean?" she asked, cocking her head to the side. Her fingers fiddled nervously with the needle held between them and he sighed again. 

"You're not...afraid of me. You don't worship the ground I walk on either. It's...refreshing." Jack explained sheepishly. "Sometimes I get tired of being the Pumpkin King. I want them to treat me like Jack too. You're the only one who sees both sides." 

"Well...I've never actually seen the Pumpkin King in action, and he only comes out one day of the year. It doesn't make sense to treat you like the Pumpkin King when you're Jack three hundred and sixty four days out of the year." Sally said with a soft smile, taking Jack's momentary stillness (because, really, the man never stopped moving) to finish her stitching on the left sleeve. 

Jack's face softened further and he waited until Sally put the needle down to draw her into a gentle hug. 

"Thank you Sally." he mumbled against her soft, fiery locks. Sally rested her cheek against his sternum briefly and smiled, returning the hug. 

"No, thank _you_ Jack." she grinned, alluding to their first meeting. Jack laughed, and with that the tender moment was over. 

Neither one noticed that they were were half in their own heads the rest of the time Jack was there. 

- **The Third Time-**

If anyone mentioned Lock, Shock, and Barrel, it was always accompanied by a shudder and dark mumbling. Sally was alarmed by it at first; they were just kids, or so she originally thought. While it wasn't unusual for the residents of Halloween Town to exhibit a sort of deviousness, the trio seemed to run the market on mischief and mayhem. Everywhere Sally sneaked off to, the trio was getting into trouble. They had poked holes in the curtains of the vampires' house, they had poured chemicals into the lake that the dark lagoon creature, who Sally had heard was called Lucinda, but wasn't quite sure*, lived in, and they had even gone so far as to try and capture one of Mr. Hyde's smaller versions in a rat trap. At first Sally had thought it was all in good fun, but then she realized that the pranks could have been quite deadly had nobody cottoned on quick enough. It was then that she also started to notice how poorly the trio was treated by everyone else in town. They were hissed at, skirted around, avoided, and the other children in the town would push them around and call them all sorts of unsavory things when they didn't think any adults were looking. They always answered with jeers and taunts of their own, and the people that were the worst to them often got the worst tricks in return, but it still bothered Sally to see three children act in such a depraved manner, especially when the adults were doing nothing about it. 

And then one day, she saw Jack talking to them. She had been sitting in the Hanging Tree, chatting with the Hangmen, when Lock, Shock, and Barrel came peeling around the corner. They looked terrified for once, which was unusual, and they slammed into each other rather comically as Lock tried to avoid running headfirst into the low wall that divided the grassy area where the Hanging Tree often stood from the cobblestone street. 

"Do you think he-" Lock began.

"You betcha." Shock panted, putting her hands on her knees to catch her breath. 

"We should probably keep-" Barrel started, but he cut himself off as Jack came stalking around the corner. 

"You three are in deep trouble this time." Jack growled, his bony hands curled into tight fists. All three whimpered, and the two boys cowered behind Shock. 

"Aw, c'mon Jack, it was all in good fun." Lock whined, albeit a bit smoothly. Jack's face only grew angrier and he shook his head. 

"Good fun?  _Good fun?_ People could have died with that prank Lock. Just like all the pranks you've been pulling lately." Jack hissed before rubbing at his face wearily. "Look...I know that you three are having trouble fitting in here," he was met with a snort from all three, "but maybe you should hang around someone other than Oogie. He's...not good for anyone." Jack continued slowly. The three exchanged a look and it was Barrel who slumped first. 

"Nobody but Oogie  _wants_ us around Jack. Can't you see that?" he murmured, his usually jovial grin gone. Sally felt something in her heart ache at the forlorn expression on his face and she slowly slid out of the branches of the tree. 

"You haven't given yourselves a chance either." Jack said softly, kneeling in front of the three trick-or-treaters. "Being new here isn't easy, but you shouldn't be making it harder for yourselves." 

"You have no idea what it's like Jack! Everyone likes  _you_." Shock huffed, her green skin flushing in anger and embarrassment. 

"I wasn't always the Pumpkin King Shock, and not everyone liked me before I claimed the throne." Jack retorted, and she folded her arms across her chest at that. "You three really need to work on being  _good_ for once. Life isn't just tricks and treats." 

The three contemplated Jack's words for a moment before nodding and taking off in the opposite direction, leaving Jack to stand up and straighten out his suit with a sigh. 

"They really are trouble, aren't they?" Sally asked, stepping out from behind the tree. Jack looked up and smiled a bit at her. 

"Yes, but I hope that they'll change someday. They could seriously hurt someone with their pranks, and I don't think that Oogie is a good influence on them." Jack said, rubbing the back of his neck. Sally walked over until she was standing beside him, both of them looking down the road that the three had disappeared down. 

"If you keep talking to them, I think they might one day." she said honestly, offering Jack a bit of a shy smile. Jack looked at her in surprise and chuckled. 

"I don't know about that. Oogie really has them in his grasp, and Oogie was never one to play fair." he murmured. Sally squeezed his hand lightly. 

"If anyone can help them, it's you Jack." Sally countered, her face shining with a firm sort of belief in Jack that he found rather refreshing. In Sally's eyes, Jack was a force of good, and if he ignored the warmth blossoming in his bones at the thought...well, he wasn't any less of a good man for it, was he?

- **The Fourth Time-**

Jack was terrified. Honestly, truly terrified. Oogie not only had Sandy Claws, but he had Sally as well. His Sally, the brilliant woman that had helped him make the best Halloween yet, the woman that had  _warned_ him that this whole Christmas thing was going to be a disaster instead of bowing to his every whim, his best friend...the fear mixed with fury and he did not hesitate to grab both Sally and Sandy from Oogie's death trap, taking their place but putting a steady foot down so that he wouldn't slide into the boiling vat of oil below. 

Sally and Sandy watched from a distance as Jack battled Oogie, and if Sally wanted to scream during most of the fight she did an excellent job at restraining herself. The skeleton was radiating a pure sort of fury that both warmed her and chilled her to the core at the same time. He was battling to protect her, to protect Sandy, and in that moment Sally knew that the warmth that fluttered in her chest every time she thought of or saw Jack was not just friendship. It was love. And she would not lose Jack again. So she called out to Jack when it looked like he might be caught by Oogie's traps and kept Sandy safe when Jack didn't need her help. 

After Jack apologized to Sandy and the man made his exit, Jack's mind finally caught up with him. The rage and fear simmered to a low boil and were washed away completely when Sally walked over to him.

"He'll fix things Jack. He knows what to do." Sally said softly, going so far as to offer him a reassuring touch on the elbow. Jack turned in amazement, the questions finally making their way through his muddled emotions.

"How did you get down here Sally?" he asked.

"Oh. I was trying to...well I wanted to...to..." she stammered, twisting her fingers together nervously.

"To help me?" Jack offered, touching a hand to his chest unconsciously. It made him feel warm, warmer than pretending to be Sandy had made him feel, even warming than reclaiming the mantle of Pumpkin King had.

"Well I couldn't let you just..." Sally offered sheepishly.

"Sally, I can't believe I never realized that you..." Jack got closer, and just as he was about to say what he had just realized, a light shone down on them both and the Mayor called out to him. The words caught in his throat; his best friend, his partner in crime, she was  _everything_ to him, and he had almost lost her. In those moments when he wasn't entirely sure if he would defeat Oogie, if he would make it out of the fight alive, he had come to realize that he loved her. Jack Skellington, the Pumpkin King, the most fear inducing creature in Halloween Town, had fallen in love. It felt cliche considering she was his best friend, but he didn't care. 

But that would have to wait; he had to make a triumphant return and make sure that Sandy fixed the damage he had caused. 

- **The Fifth Time-**

Sally's heart was consumed by the emotion she had just so recently accepted when the Mayor drove them back into Halloween Town. The citizens were so thrilled to see that Jack was alive, and the sight of little Ethan clinging to his bony leg made her want to swoon. Jack was so good for Halloween Town, and good in general. He was smart, brave, and dedicated...she sat in the front of the Mayor's hearse almost dumbly and watched as the town dissolved into almost delirious celebration. When the snow began to fall, she took the opportunity to slip away to Spiral Hill, her favored thinking spot. She needed to figure out what she was going to do now that the situation had certainly changed. 

Jack had been a bit overwhelmed by the town's reaction if he was being honest with himself, and he was grateful for the distraction that the snow provided. His skull was buzzing yet again, but this time the overriding thought was to find Sally. He had gotten a bit sidetracked in that mission, but when he saw the doctor with his new creation, his heart gave a leap and he gaped for a moment before looking around frantically. He turned his head just in time to see Sally slip through the gate towards the cemetery and beyond and he took the opportunity to sneak away after her. 

His breath was sucked out of his chest as he saw her sitting on that hill, plucking the petals of a flower off in a warped game of 'he loves me, he loves me not". Her hair gleamed in the light of the moon and he wanted to scoop the fallen petals up and push half them back into her hand, whisper that 'he loves you, the petals that say I don't can rot", kiss her senseless. Instead, he called out to her in the only way he knew how. Walking up quietly, he cleared his throat. 

"My dearest friend, if you don't mind...I'd like to join you by your side. Where we can gaze into the stars..." he sang out. 

"And sit together, now and forever." Jack and Sally both felt their hearts would burst; they were in unison, their minds and hearts finally,  _finally_ catching up to one another. "Now and forever. For it is plain as anyone can see, we're simply meant to be." 

As they joined hands and their eyes met, they both knew that they were in the right place. It wasn't just their personalities that meshed perfectly, their cleverness, but the timing of everything. Had Sally not been created before Jack had fallen into his funk, had Jack not stumbled upon Christmas Town and lost himself in the madness of it all, had Sally not been brave enough to try and rescue Sandy...they wouldn't have fallen together like this. It overwhelmed them both a bit, and they moved in on one another, their lips finally meeting in a sweet, gentle kiss that sent both of their hearts racing and shut both of their minds down for just a moment. 

"I love you." Jack whispered, tucking a strand of her hair behind her ear once they parted. Sally smiled widely, offering Jack her most lopsided grin yet, and she blushed darkly. 

"I love you too Jack." she murmured in reply, and everything felt right in Halloween Town for just a moment. 

- **Now and Forever** - **  
**

Each year after that, Sandy swept by on Christmas night, coating Halloween Town in a thick layer of snow that would last them until spring. In those months, when Halloween took a bit of a spot on the back burner (for everyone but the Mayor at least), Jack and Sally were perfectly content to bundle up in Jack's huge house and hide away from the cold. However, two years after Jack had turned Christmas upside down for the human world, he was not tucked away in front of a fire when the snow fell. Instead, he was setting out clues for Sally to follow, clues that would lead her to the Hill. Notes that were tied to the doorknobs, pictures strung along fences, pieces of paper given to Halloween's finest trick-or-treaters, all of which led Sally on an elaborate goose chase around the town. 

By the time she made it to the Hill, the moon was high in the sky and Jack was shivering despite the warm, thick, black and white striped sweater that Sally had knitted him when they realized Sandy was intent on making it snow  _every_ Christmas. He still painted a perfect picture in her eyes, tall, thin, elegant, slightly dark even as he stood in the moonlight. Her breath hitched in her chest faintly and she stalked up the incline with a grin on her face. 

"Jack, what is all this?" she asked, holding up the rather thick stack of paper she now had in her hands. Jack smiled broadly and shifted from foot to foot. 

"My dearest friend, if you don't mind, I'd like to join you by your side...where we can gaze into the stars..." he began, and Sally blushed, her smile only growing. She didn't join in though; something felt off about it this time. 

"And sit together now and forever, for it is plain as anyone can see; we're simply meant to be." Jack finished, his bony fingers dipping into his pocket briefly. By the time the last note was leaving his lips, he was on one knee, holding up a ring. It was black metal and the stone was a glittering black diamond with little white diamonds decorating the elaborately crossed band beneath the stone. The beauty of the ring stunned Sally for a moment before she was consumed by the love and hope written across Jack's face. A tear rolled down her cheek and she dropped to her knees, wrapping her arms around his neck and pulling him in for a hug. The kissed briefly, a mirror of the first kiss they had shared on this hill, and she barely noticed as he slipped the ring onto her finger, she so wrapped up in staring into his eyes and pressing their foreheads together. 

"Now and forever." she murmured, squeezing him once more and laughing when he pushed her into the snow, his joy showing itself in playfulness and the almost blinding grin he wore. 

**Author's Note:**

> *The Fabulous Dark Lagoon Creature is only named as such in the movie, and is referred to on the Nightmare wiki as that and 'Undersea Gal'. I thought she needed a name for this so I made one up. 
> 
> Also, the cheeeeeeeeese at the end. I'm sorry. I needed to do it. I NEEDED IT.


End file.
